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5-MeO-DALT

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5-MeO-DALT
Clinical data
Other namesN,N-Diallyl-5-methoxytryptamine; 5-Methoxy-N,N-diallyltryptamine; 5-Methoxy-DALT; Foxtrot
Routes of
administration		Oral[1]
Drug classSerotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics)[2]
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • UN: Unscheduled.
  • In general unscheduled and not approved for human consumption, Illegal in China, Japan, Singapore, Sweden, Florida and Louisiana
Pharmacokinetic data
Duration of action2–4 hours[1]
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H22N2O
Molar mass270.376 g·mol−1
3D model (JSmol)
  • C=CCN(CCC1=CNC2=C1C=C(OC)C=C2)CC=C
  • InChI=1S/C17H22N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h4-7,12-13,18H,1-2,8-11H2,3H3 checkY
  • Key:HGRHWEAUHXYNNP-UHFFFAOYSA-N checkY
  (verify)

5-MeO-DALT, also known as N,N-diallyl-5-methoxytryptamine or as foxtrot, is a psychedelic drug of the tryptamine and 5-methoxytryptamine families.[1][3] It was first synthesized and described by Alexander Shulgin, who disclosed the compound in 2004.[1][4] The drug has been encountered as a novel designer and recreational drug.[4][5]

Dosage and effects

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According to Alexander Shulgin, the dosage of 5-MeO-DALT is 12 to 20 mg orally and its duration is 2 to 4 hours.[1][6] A wider dose range of 12 to 25 mg has also been reported.[7] It is said to onset and peak remarkably quickly via the oral route, with an onset of less than 15 minutes and a peak of 30 minutes.[1] The effects of 5-MeO-DALT were reported by Shulgin to include positive emotional changes, lightheadedness, increased appreciation of music and sex, and closed-eye visuals.[1] There was said to be a lack of open-eye visuals and it was said to be relatively light in psychedelic character.[1]

Side effects and overdose

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There is little published literature on the toxicity of 5-MeO-DALT.[8] Case reports of overdose have been published, with effects including loss of consciousness, visual hallucinations, acute delirium, and rhabdomyolysis, among others.[8][9][10] A death related to behavioral intoxication has been reported.[3]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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5-MeO-DALT activities
Target Affinity (Ki, nM)
5-HT1A 3.26–48 (Ki)
3.4 (EC50Tooltip half-maximal effective concentration)
102% (EmaxTooltip maximal efficacy)
5-HT1B 735
5-HT1D 107
5-HT1E 500
5-HT1F ND
5-HT2A 71.7–218 (Ki)
11.3–139.4 (EC50)
97–114% (Emax)
5-HT2B 59
5-HT2C 456–573 (Ki)
299 (EC50)
99% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 3,312
5-HT6 153
5-HT7 90
α1A–α1D >10,000
α2A 215
α2B 726
α2C 1,467
β1–β3 >10,000
D1–D5 >10,000
H1 505
H2 4,250–>10,000
H3 1,712 (guinea pig)
H4 >10,000
M1–M5 >10,000
nAChTooltip Nicotinic acetylcholine receptor >10,000
I1 ND
σ1 301–398 (rat/guinea pig)
σ2 253 (rat)
TAAR1Tooltip Trace amine-associated receptor 1 ND
MORTooltip μ-Opioid receptor, DORTooltip δ-Opioid receptor >10,000
KORTooltip κ-Opioid receptor 1,132
SERTTooltip Serotonin transporter 499–1,189 (Ki)
>100,000 (IC50Tooltip half-maximal inhibitory concentration) (rat)
22,313 (IC50) (human)
>100,000 (EC50) (rat)
NETTooltip Norepinephrine transporter >10,000 (Ki)
>100,000 (IC50) (rat)
>100,000 (EC50) (rat)
DATTooltip Dopamine transporter 3,378 (Ki)
>100,000 (IC50) (rat)
>100,000 (EC50) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [11][12][13][14][15][16][17][18][19]

The interactions of 5-MeO-DALT with various targets have been reported.[13][14][15][19][17] It binds to a variety of serotonin receptors, as well as a number of other targets.[13][14][15][19] The drug is a potent full agonist of the serotonin 5-HT1A and 5-HT2A receptors.[15][16][18][17] It is also an agonist of the serotonin 5-HT2B and 5-HT2C receptors.[16]

Similarly to other psychedelics, 5-MeO-DALT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[7][15][14] The drug fully substitutes for the serotonergic psychedelic DOM in rodent drug discrimination tests.[20] Conversely, 5-MeO-DALT does not substitute for the entactogen MDMA in such tests.[20] 5-MeO-DALT produces dose-dependent hyperlocomotion in rodents, followed by hypolocomotion at the highest assessed dose.[20][15] This is in contrast to many other psychedelic tryptamines, which tend to produce only hypolocomotion.[20] 5-MeO-DMT and 5-MeO-AMT are locomotor depressants, whereas 5-MeO-DET and 5-MeO-MiPT are mixed locomotor stimulants/depressants similarly to 5-MeO-DALT.[20] It also produces hypothermia.[15]

The head-twitch response induced by 5-MeO-DALT in rodents was found to be positively related to its serotonin 5-HT2A receptor affinity and negatively related to its serotonin 5-HT1A receptor affinity.[14] In relation to this, multiple targets appear to contribute to the effects of 5-MeO-DALT.[14][5]

Pharmacokinetics

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The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.[21][22]

Chemistry

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The full name of the chemical is N-allyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl] prop-2-en-1- amine. It is related to the compounds 5-MeO-DPT, DALT, 4-HO-DALT, and 4-AcO-DALT.

In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT.[23]

History

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The first material regarding the synthesis and effects of 5-MeO-DALT was sent from Alexander Shulgin to a research associate named Murple in May 2004, after which it was circulated online. In June 2004 5-MeO-DALT became available from internet research chemical vendors after being synthesized by commercial laboratories in China. In August 2004 the synthesis and effects of 5-MeO-DALT were published by Erowid.[4] Shulgin has stated that 5-MeO-DALT had not previously existed in the scientific literature.[1] 5-MeO-DALT was not included in the original published version of TiHKAL, but an entry for the compound was subsequently written and released in 2004.[4]

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China

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As of October 2015 5-MeO-DALT is a controlled substance in China.[24]

Japan

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5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.[25]

United Kingdom

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5-MeO-DALT became a Class A drug in the UK on January 7, 2015 after an update to the tryptamine blanket ban.

Singapore

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5-MeO-DALT is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.[26]

Sweden

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Sveriges riksdag added 5-MeO-DALT to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of May 1, 2012, published by Medical Products Agency in their regulation LVFS 2012:6 listed as 5-MeO-DALT N-allyl-N-[2-(5-metoxi-1H-indol-3-yl)etyl]-prop-2-en-1-amin.[27]

United States

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5-MeO-DALT is not scheduled at the federal level in the United States,[28] but it is likely that it could be considered an analog of 5-Meo-DiPT, which is a controlled substance in USA, or an analog of another tryptamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

Florida

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5-MeO-DALT is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[29]

Louisiana

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5-MeO-DALT is a Schedule I controlled substance in the state of Louisiana making it illegal to buy, sell, or possess in Louisiana.[30]

Research

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Cluster headache

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Anecdotal reports[31] and a small-scale trial[32] indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine.[33] These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache.[34]

See also

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References

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  1. ^ a b c d e f g h i "#56 5-MeO-DALT". Isomer Design. Retrieved 28 March 2025.
  2. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. ^ a b Corkery JM, Durkin E, Elliott S, Schifano F, Ghodse AH (December 2012). "The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5-methoxytryptamine): a brief review". Prog Neuropsychopharmacol Biol Psychiatry. 39 (2): 259–262. doi:10.1016/j.pnpbp.2012.05.022. PMID 22683457.
  4. ^ a b c d Morris H, Smith A (2010-05-02). "The Last Interview With Alexander Shulgin". VICE.
  5. ^ a b Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524. The N,N-disubstituted compound 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT 18) has recently appeared as a new "legal high" on the illicit market (Corkery et al. 2012; Strano Rossi et al. 2014). Results from broad-based receptor screening led Cozzi and Daley (2016) to conclude that multiple serotonin receptors, as well as several non-serotonergic sites are important for the psychoactive effects of 18 and other N,N-diallyltryptamines.
  6. ^ Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs. Archived from the original on 2021-12-13. Retrieved 3 September 2015 – via YouTube.
  7. ^ a b Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167: 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]
  8. ^ a b Dufayet L, Langrand J, Alvarez JC, Islam Larabi A (August 2022). "Loss of Consciousness and Visual Hallucinations Related to 5-MeO-DALT Intake, a Case Report Confirmed by Toxicological Analyses". J Anal Toxicol. 46 (7): e186 – e190. doi:10.1093/jat/bkac021. PMID 35365824.
  9. ^ Kalasho A, Vibe Nielsen S (October 2016). "5-MeO-DALT; a novel designer drug on the market causing acute delirium and rhabdomyolysis". Acta Anaesthesiol Scand. 60 (9): 1332–1336. doi:10.1111/aas.12765. PMID 27453155.
  10. ^ Jovel A, Felthous A, Bhattacharyya A (May 2014). "Delirium due to intoxication from the novel synthetic tryptamine 5-MeO-DALT". J Forensic Sci. 59 (3): 844–846. doi:10.1111/1556-4029.12367. PMID 24329118.
  11. ^ "Kᵢ Database". PDSP. 28 March 2025. Retrieved 28 March 2025.
  12. ^ Liu T. "BindingDB BDBM50435344 CHEMBL2391541". BindingDB. Retrieved 28 March 2025.
  13. ^ a b c Cozzi NV, Daley PF (February 2016). "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines" (PDF). Bioorganic & Medicinal Chemistry Letters. 26 (3): 959–964. doi:10.1016/j.bmcl.2015.12.053. PMID 26739781.
  14. ^ a b c d e f Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs" (PDF). Neuropharmacology. 142: 231–239. doi:10.1016/j.neuropharm.2018.02.028. PMC 6230509. PMID 29499272.
  15. ^ a b c d e f g Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC 11412900. PMID 38486047.
  16. ^ a b c Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S (June 2013). "An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'". Bioorg Med Chem Lett. 23 (11): 3411–3415. doi:10.1016/j.bmcl.2013.03.066. PMID 23602445.
  17. ^ a b c Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter" (PDF). J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  18. ^ a b Pottie E, Cannaert A, Van Uytfanghe K, Stove CP (December 2019). "Setup of a Serotonin 2A Receptor (5-HT2AR) Bioassay: Demonstration of Its Applicability To Functionally Characterize Hallucinogenic New Psychoactive Substances and an Explanation Why 5-HT2AR Bioassays Are Not Suited for Universal Activity-Based Screening of Biofluids for New Psychoactive Substances". Anal Chem. 91 (24): 15444–15452. doi:10.1021/acs.analchem.9b03104. PMID 31725281.
  19. ^ a b c Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  20. ^ a b c d e Gatch MB, Dolan SB, Forster MJ (August 2017). "Locomotor and discriminative stimulus effects of four novel hallucinogens in rodents". Behav Pharmacol. 28 (5): 375–385. doi:10.1097/FBP.0000000000000309. PMC 5498282. PMID 28537942.
  21. ^ Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH (October 2015). "Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MSn, and LC-HR-MS-MS" (PDF). Analytical and Bioanalytical Chemistry. 407 (25). Springer Science and Business Media LLC: 7831–7842. doi:10.1007/s00216-015-8955-0. PMID 26297461. S2CID 26086597.
  22. ^ Dinger J, Woods C, Brandt SD, Meyer MR, Maurer HH (January 2016). "Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class" (PDF). Toxicology Letters. 241. Elsevier BV: 82–94. doi:10.1016/j.toxlet.2015.11.013. PMID 26599973. S2CID 2384720.
  23. ^ Chadeayne AR, Pham DN, Golen JA, Manke DR (April 2020). "5-MeO-DALT: the freebase of N,N-diallyl-5-meth-oxy-tryptamine". IUCrData. 5 (Pt 4). International Union of Crystallography (IUCr): x200498. Bibcode:2020IUCrD...500498C. doi:10.1107/s2414314620004988. PMC 9462216. PMID 36338299.
  24. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  25. ^ "厚生労働省：平成１8年度無承認無許可医薬品等買上調査の結果について" (in Japanese). Retrieved 24 July 2015.
  26. ^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  27. ^ Rångemark Åkerman CR (20 April 2012). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF) (in Swedish). Retrieved 3 September 2015.
  28. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  29. ^ "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.
  30. ^ "Louisiana State Legislature". Retrieved 3 September 2015.
  31. ^ Post M (2015). "Cluster Headache Patient Survey: 5-MeO-DALT". Figshare. doi:10.6084/M9.FIGSHARE.1372467.V3.
  32. ^ Post M (2014). "Treatment of Cluster Headache Symptoms using Synthetic Tryptamine N,N-Diallyl-5 Methoxytryptamine". Figshare. doi:10.6084/M9.FIGSHARE.1119697.V1. S2CID 73807327.
  33. ^ Brandt RB, Doesborg PG, Haan J, Ferrari MD, Fronczek R (February 2020). "Pharmacotherapy for Cluster Headache". CNS Drugs. 34 (2). Springer Science and Business Media LLC: 171–184. doi:10.1007/s40263-019-00696-2. PMC 7018790. PMID 31997136.
  34. ^ Schindler EA, Gottschalk CH, Weil MJ, Shapiro RE, Wright DA, Sewell RA (2015-10-20). "Indoleamine Hallucinogens in Cluster Headache: Results of the Clusterbusters Medication Use Survey". Journal of Psychoactive Drugs. 47 (5). Informa UK Limited: 372–381. doi:10.1080/02791072.2015.1107664. PMID 26595349. S2CID 21948146.
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